Taming the Dragon
by wagahaiwaneko
Summary: Kyouya, against every pillar he's ever stood up for, falls for a commoner with no heritage and a radical, free-spirited way of doing business. Here's the story of how a Silicon Valley start-up princess brought the Shadow Lord to his knees. [Set years after HS graduation, Kyouya/OC]
1. Chapter 1

**Taming the Dragon: How Kyouya Met His Match**

_Kyouya, against every pillar he's ever stood up for, falls for a commoner with no heritage and a radical, free-spirited way of doing business. Here's the story of how. [Set after graduation, Kyouya/OC]_

* * *

It all started at Stanford. It was that damned lecture – the lecture that changed Kyouya's life, for better or for worse (for better, as his wife likes to say).

It had been any old day in class at the Stanford Graduate School of Business - or so Kyouya had thought. He'd originally come to the university after his undergraduate stint at Harvard in Boston – Haruhi had completed her degree the year after and Kyouya left the East Coast as Tamaki's visits became more frequent. Best friends or not, it was still important to keep one's personal space, especially when one had a Japanese-Frenchman flying in every weekend to crash on Kyouya's couch, in order to visit his girlfriend.

In any event, Kyouya's studies in Asia-Pacific business led him westward, where he found himself the rising star at the Stanford Business Magazine. At the top of his class (naturally), he was destined for success. But he knew that – weren't his Ouran years played out in the same fashion? He continued networking and expanding his capabilities, knowing his father would notice.

However.

_She_ happened. _She_ was also looking over his shoulder just as he was typing this part of their story out – and _she_ said to make sure Kyouya took proper account of their tale and removed his bias. Kyouya told her he'd try.

Anyway…

As mentioned before, that morning during his second year of business school was, as to be expected, business as usual. He knew precisely that his business model course was having yet another prolific guest lecturer today: a certain venture capitalist from the Silicon Valley, who'd had a hand in all the leading search, social network, and technology companies at the top of the pyramid today. He had been expecting middle-aged, brown-haired man.

The minute before the class began should have alerted Kyouya. Usually, with guest lecturers, the resident professor and his visiting colleagues would already be situated in the front of the lecture hall, conversing with each other and catching up. And knowing the professor, this was always _at least_ five minutes before lecture really began – precisely why Kyouya always showed up 10 minutes early.

One couldn't miss a networking opportunity, right?

But today, the lecture hall was virtually empty, save for a few of his like-minded but far subordinate classmates.

Three minutes passed after the official class start time.

Kyouya glanced down at his watch. No, the time was right – but the lecturer wasn't.

And then the door banged open, with a breathless, bright-eyed twenty-something running in. He scoffed. A student he'd never seen had the _nerve_ to come late to a class she'd never shown up in before? Well, she certainly picked the right day to do it. There wasn't a lecture anyway….

Kyouya's critical thoughts petered off as he saw the girl pull out a slim, top-of-the-line laptop and put it on top of the lecture podium.

"Sorry I'm late!" chirped the brunette, obviously-half-Asian woman. She seemed to be about 5 foot 8, lean from fitness and presumably the Californian organic diet, and had long (almost unkempt) wavy hair. She was wearing somewhat respectable clothing – khaki capris and a relaxed blouse with the sleeves rolled up – but she was also wearing flip-flops. "I know you were expecting a big fancy venture capitalist, but I was called this morning by your professor to give an emergency lecture! Turns out the other guy had an emergency flight out to New York last night."

The lecture hall stayed silent. This was partially because they knew who she was, and partially because they couldn't be sure until she introduced herself.

The girl swept the lecture hall with her eyes. She was obviously very energetic and bright – but perhaps not so much! It took her a few minutes before she blinked, surprised, and laughed. "Oh! Sorry. I don't suppose I've introduced myself yet." She grinned, jumping down from the lecture hall's stage and sitting on the edge of it, to be closer to the students. "I'm Alex Mirai Tomoya, short for Alexandra" (she pulled a face) "and I'm founder and CEO of DataBank – I'm here today as your guest lecturer because today's topic is on Successful Startups: Recipe for Riches, right?"

Her audience nodded.

"Cool! Let's get started, then."

Kyouya pursed his lips, then like a diligent student, he began taking notes.

* * *

Much to his disdain, this Alex girl was a visionary. She'd seen the need for a bridge between corporations and consumers where others had tried and failed – DataBank was essentially an encryption service that served two ends of the client spectrum: B2B and B2C. It served as a secure digital highway for consumer information – even hi-risk information like bank account numbers, passport information, and permanent address histories – to be given to companies without any identifiers that would jeopardize the consumer. It gave the companies the information they needed to make informed marketing strategies, but also gave consumers a single platform for them to upload their information. The encryption was military-grade, as far as anyone knew, and was in the talks of being used on a large-scale overseas.

It made absolutely no sense – this overly casual girl couldn't be more than 25 (Kyouya's age), and yet she now sat atop the digital privacy throne. Kyouya took great notes, but also seethed through the whole lecture. It was impossible, and he was damned if he didn't get to the bottom of this.

* * *

"Bye! Yeah, thanks for being a great participant! No, I totally welcome questions. Oh, unfortunately I can't give you my personal email thanks to the weird stuff that comes with sudden success, but you can call my office and have a chat!" Alex wrapped up questions, interacting with each student on their way out the door.

One student lingered. As she turned to pack up her things, she noticed Kyouya standing before her. "Oh! Hi," she grinned, extending a hand. "Kyouya, right?"

Kyouya was briefly stunned – how had she known who we was? Wait, no. He had begun to gain popularity in Japan as the new "economic prince" – one who the business media was clamoring to take over the Ootori throne. His brothers now felt the pressure he'd always had to deal with. The heir apparent to Ootori power was now no longer apparent.

So, he simply smiled and shook her hand. "Correct. I'm delighted to meet you; it was certainly an interesting lecture."

"I'm glad you think so!" Alex heaved a sigh of relief. "You know, business school attracts so many people who've been in the workforce for a few years, so it was really great to see a friendly, younger face in the audience!" She paused, as if to collect her thoughts. "You're Harvard 2012, right? I'm Cambridge 2011! Same year."

Kyouya hid his surprise. He'd read about her in the papers (vaguely – he'd initially dismissed her as a one-hit-wonder, but after her lecture it seemed that DataBank had even greater potential than it currently showed) but never imagined her to be around same age as him – and _lecturing_ about business strategy.

"Oh?" He said. So she was older than him. Perhaps the one year was her advantage – damn him for being born one year too late! "You're 26? Rather impressive portfolio for someone so young."

Alex simply laughed. "Nope! I'm 24! I took some easy credits at the local community college while I was still in high school – then my IB credits transferred over. So I started at Cambridge a year early – and once I started figuring out a project that became DataBank, I was so inspired that I took more classes over the summer so to graduate in 3 years. I guess that…" she frowned a little, doing the math. "…that makes it two years? Since I compiled the founding team of programmers? Yup, two years."

Kyouya smiled wanly. She was the impossible girl. How could she have done all that? She'd briefly mentioned that her degree was in something flippant, like Philosophy, and that she grew up in a middle-class, suburban family. "What a great story. And a great lecture!" He did his best to keep his elegant poise.

Oddly enough, Alex rolled her eyes at him. "Sure, whatever. But tell me about you! I mean, your story's amazing. You're up in the running to inherit your family's giant business, right? I know enough about Japanese culture to know that's an impressive mark for a third son, even though I'm third-generation American-born. You're all over Japanese papers!"

Kyouya raised his eyebrows. "Am I? I'm curious – how did you find out about me? You seem to know quite a lot."

A nervous giggle left Alex's lips. "I don't think that's important… but suffice it to say, you're gaining a lot of public support from the biz world. Congrats!" She smiled.

"Is that so? How interesting. At any rate, I came up to ask you more about your rise to success at such a young age. I'm assuming you know the layout of Stanford's campus – walk with me to the café?" Right now, Alex was a big variable. A big mess, thrown into his life. She unsettled him in a way that made Kyouya uncomfortable – how could she be so successful already? In fewer years than he – he hadn't even achieved his summit yet!

And whenever Kyouya became conscious of a threat, of the unknown…. Well, it was his mission to find out more. Knowledge was key to his triumph – and he needed to know more about here.

Was she an asset? A foe to be defeated? He stole a glance at her out of the corner of his eye as they walked along the gorgeous paths. At her height, she certainly was a formidable opponent. DataBank's potential wasn't a threat to the Ootori Group – but it was highly likely that an early deal would benefit their healthcare data supply immensely.

He had always loved a good challenge – but this time, he began to be unsure that he'd come out on top.

Who _was_ Alex Tomoya? For Kyouya, she was a complete and utter mystery.


	2. Chapter 2

**Taming the Dragon: How Kyouya Met His Match**

_Kyouya, against every pillar he's ever stood up for, falls for a commoner with no heritage and a radical, free-spirited way of doing business. Here's the story of how. [Set after graduation, Kyouya/OC]_

* * *

From Alex's point of view, Kyouya was a fascination - and certainly not a mystery. Her infatuation with him had begun early; being the oddly prodigious child of awesome, but relatively normal parents had made quite a few enemies of her school friends, so she'd always been inspired by people around her age who defied societal norms while simultaneously gaming them to their advantage.

Consider it a weird obsession with talented chess players... Except chess wasn't chess - chess was real life.

Nevertheless, she had stumbled across Kyouya in one of her rare spend-the-whole-workday-Googling-things days. She'd been aiming to do research on potential up-and-coming clients for DataBank, and healthcare (among military/government and other SaaS companies) was always one of the top industries on her to-get list.

She wasn't a stalker. It was simply professional curiosity. Right? Right.

At any rate, what had started off as reading articles about Ootori Group (headlines screamed "The Third Son Defies Tradition and Overhauls the Company!" and "Japan's Medical Industry Soaring to New Heights with Ootori!") had quickly degenerated to paparazzi image search (there were very few real-life photos of Kyouya online, but a great many of him in suits, speaking before people), and eventually reading Japanese gossip rags about "The Most Eligible Bachelors of Tokyo" - to which Kyouya (and of course most of Ouran's elites) belonged to the top 10.

Yup - Alex was smitten. Her fascination with his successes had ignited the attraction, but Kyouya was certainly a handsome one...

But perhaps it would benefit Kyouya's narration to mention just why Alex had been so keenly interested in someone she'd never met (this addendum to this narrative comes at the request of Kyouya's pestering wife).

* * *

Those childhood enemies? They were, of course, the popular girls at school - and some of the intelligent guys. Alex had been lucky to be born with her brain, and her luck was a fact she reminded herself of daily. She had been given interesting opportunities to showcase her intelligence with many thanks to the relentless support and help from her parents. There was no silver spoon - just luck. But no matter how many efforts Alex had made as a child to hide her intelligence and fit in, there was no way around it.

People wouldn't like her. The nerdy, intelligent boys felt threatened by her and turned the computer science clubs into hostile, masculine environments - but the girls didn't like that someone was getting so much attention in the local and national news for her achievements. Nevermind that her achievements had nothing to do with the areas of expertise of her bullies; recognition was recognition, and the mousy girl with more brains than beauty was getting more of it than the bottle-blonde eyeliner perfectionists of her high school.

Alex had been an outcast. And part of her attraction to Kyouya was that he, too, seemed to offer this narrative of being outside of the mold - and yet, it seemed early on that he had learned to manage the rules of high society and seemingly play by them.

That was what mystified her first. He was still admired, even if he was feared, but Alex - up until the start of DataBank - had simply been feared or ignored.

Three years ago, Kyouya's story had become her inspiration to pretend to play by society's rules - to learn how to put on eyeliner properly and to make grating (but necessary) small talk - while also breaking them along the way.

* * *

Sentimental and mildly obsessive stories aside (the narrator has been told to strike the word "obsessive" from the record, but he chooses to retain it because _it is the truth_), the point was that Kyouya's coffeeshop meeting with Alex began a period in his life where He Was Chased By A Woman And Actually Liked It (Eventually).

The unfortunate reality of that period was that Kyouya thought he had the upper hand the entire time - and only realized how deep he had gotten a bit later than ideal.

When he asked her to walk with him, it was not to ask her on a date, although she would take great pains to say that yes, it was. It was to gather intel on the infuriatingly talented and overly chirpy woman.

You'd think that Kyouya was used to overly talented airheads being in his life; after all, he had several years of experience with Tamaki Suoh, Interim Superintendent of the Ouran School System, but apparently that wasn't enough.

Maybe it was the fact that the duty of pandering to Tamaki's whims had passed on to a certain ex-crossdresser after certain "I do's" were said - or maybe it was that the "I do's" also coincided with Kyouya's move to California after four years in Boston.

Whatever it was, Kyouya was unprepared for the female version of his best friend to take a vested interest in him.

* * *

Kyouya impatiently drummed his fingers on the table as this Alex person prattled on and on about the fun of data science and her inspiration to abandon philosophy in favor of technology. It was all fine and good, but it was nothing that Kyouya couldn't deduct from a cursory Google search on his phone during the lecture.

No, what he wanted to know was _how_ she had the personal strength to barrel through her ambitions without pedigree.

"So what about your background?" He asked coolly, tilting his chair back and cutting her off mid-sentence. "What about your past kept you going despite the odds?"

The girl's smile faltered, and Kyouya noted the emotions flickering through her expressions. First there was a brief glimpse of pain, then a flicker of memory and comprehension, then suspicious nervousness. Alex completed her opera of emotions by settling for a contemplative look.

"Well... I'm assuming you're asking how I could have beaten you to the achievement punch, right?"

Kyouya would have choked on his coffee were it not for the years of composure he'd built up by proxy of being in the same room as Tamaki. "Mmm..." _Think of a higher-handed comeback, fast! _"I don't think that's quite it. Different personal circumstances affect different outcomes."

Alex raised an eyebrow. Kyouya's response was collected, smooth, and political. She was impressed - she expected nothing less calculated than that. Still, despite her excitement in meeting one of her greatest inspirations, she also had an image to upkeep.

"I'm sure after six years back-and-forth between America and Japan, you've realized that the capacity for meritocracy is greater here than it is back home." Alex sipped her iced coffee, pretending to take some more time to process her response. "It's flawed, of course, but if one is lucky enough to be blessed with an abnormally high IQ and has parents who support her no matter what, then they can defeat the odds - or at least have people around that tell her to apply for national competitions."

Kyouya nodded slowly. It wasn't a satisfactory response, but-

Wait.

Six years? Back and forth? He knew Alex had mentioned his Harvard education - it was already odd that of all things she had remembered such an irrelevant detail about him. Six years? She knew he'd been managing the Ootori connections in San Francisco before coming to Stanford? It wasn't _odd_ that someone knew about him, but it was odd that she had such lucid detail about him.

"Yes," he began carefully. "Six years. Enough time to observe the boisterousness of Americans and the stiffness of the Japanese. All stereotypes, but not without a grain of truth."

Alex nodded, suddenly aware that she had said too much. Damn! She didn't want to come off as a creep - goodness knows how desperate she was to put her awkward and lonely past behind her.

"E-exactly," she faltered. "There was more capacity for me to beat the odds through national competitions and awards, and more easily breakable societal rules." _That, and I escaped by running off to college early in another country. _But she didn't have to add that out loud.

Kyouya sighed slightly, peering down at his watch. The conversation hadn't been as enlightening as he'd hoped, but in the least it seemed the girl was more than receptive to speaking with him. That was his opening to put work towards a partnership - DataBank would be an excellent addition to the management system the Ootori hospitals already used. The headlines would be satisfactory, and the partnership would cement his rightful place as Ootori heir. Technology was the future - he had to bring Ootori Group to the cutting edge.

"Here." He slid his business card across the table, fighting every instinct to give it to her in the overly polite, two-handed Japanese way (she was younger than him, not culturally Japanese, and also uninteresting now that he realized her success was somewhat based on luck - so there was no need for polite niceties). "I'm sure you saw this coming, but I'd like to stay in contact."

Her heart soared. Her savior - her idol - wanted to keep in touch?

"That is, of course, to discuss potential avenues for integrating DataBank's technology with the information management of the Ootori Group."

...Nevermind.

* * *

Alex took the business card, offering Kyouya one of her own. She had to admit to herself that she was slightly crestfallen - she'd wanted to become his friend, not his business partner. After all, he was a great source of inspiration to her. But if that was the direction he wanted to take, then it wasn't her position to push for friendship.

It looked like loneliness was her specialty.

"Thanks. I think integrating our systems would be mutually beneficial." Alex plastered a cool look on her face, quelling the emotion beneath the surface. It felt weird - she was an earnest person, and pretending to a detached businessperson was always uncomfortable to her.

Kyouya smirked, reading the look on her face and seeing the body language that was obviously too forced. Even if she wasn't as intriguing as he'd hoped, the joint work would be amusing in the least.

He rose, offering his hand. "It's been a pleasure to meet you;I look forward to our collaboration."

Alex wanted to glare at him - in the span of an hour, he'd crushed her enthusiasm beneath his heel because he wanted to play by the rules. Fine. She could do that too. "And you as well." She shook his hand, grabbed her purse, and stormed off to her office.

Kyouya watched her back intently. She'd started off seeming to him like a female Tamaki, but as his demeanor changed, so had she. Did she really think she could match him, par for par, without the extensive training he had in business personality?  
Perhaps it would be an interesting partnership after all. She was bound to be clumsier than he, especially when taking the deal back to his home turf. There, she would see - where she really stood next to the competition.

Toying with the little business card in his fingers, Kyouya grinned. He hadn't encountered such a refreshing opportunity in a while, what with Tamaki domesticated and his destruction of worthy competitors in Japan.

He would, he decided, get back in control.

* * *

**A/N: Hope you enjoyed Chapter 2! It's been a while since I updated this, but I'm excited to be writing something more lighthearted (I've got a few more serious fics, so it'll be refreshing to write more closely to the style and cadence of the anime - the manga gets really serious). Please leave comments and reviews - authors thrive off of feedback; it's where we get the motivation to continue and improve!  
**

**Disclaimers as usual. **


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